Acetic Acid → HCID 67212465, compound

HRID 554590Notes

Reaction equation

HRID 554590 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:10]=O.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:12]([NH:19][CH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[Br:1])[C:6]#[N:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 225749024-Bromo-3-formylbenzonitrile

Product 1

HCID 67212465HCID 67212465, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-bromo-3-formyl-benzonitrile (2.42 g, 11.5 mmol) in MeOH (450 mL) was added benzylamine (1.88 mL, 17.3 mmol) and sodium cyanoborohydride (1.09 g, 17.3 mmol). Acetic acid (0.99 mL, 17.3 mmol) was added dropwise, and the reaction was stirred at room temperature overnight. The mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were dried, concentrated, and purified by silica gel chromatography (0-30% EtOAc in hexanes) to give 3-(benzylamino-methyl)-4-bromo-benzonitrile.

Workup

  1. customThe mixture was quenched with H2O
  2. extractionextracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f3b1f7eb08694b4fa6ae88192e7e622e
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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